One-pot synthesis, characterization, and antioxidant capacity of sulfur- and oxygen-substituted 1,4-naphthoquinones and a structural study

Abstract

In the present study, we reported the onepot synthesis of S,S-and S,O-substituted 1,4-naphthoquinones, their structural studies, and investigation of their antioxidant activity. The multicomponent reactions of 2,3-dichloro-1,4-naphthoquinone with sulfur-and oxygencontaining nucleophiles were investigated to obtain highly functionalized S,S-and S,O-substituted 1,4-naphthoquinone derivatives. All new compounds were characterized on the basis of 1 H, 19 F, and 13 C nuclear magnetic resonance spectroscopy, mass spectrometry, and Fourier transform infrared spectroscopy. Crystal structure of 2,3-dihydro-2-(hydroxymethyl)naphtho[2,3-b]-1,4-oxathiin-5,10-dione was determined by X-ray diffraction method. The synthesized compounds were screened for their antioxidant capacity and free radical scavenging activity using the cupric reducing antioxidant capacity method and DPPH method, respectively. 3-Chloro-2-[3-(3-chloro-1,4-dihydro-1,4-dioxonaphthalen-2-yloxy)propylsulfanyl]-1,4-naphthoquinone shows the highest antioxidant capacity with 0.63 cupric reducing antioxidant capacity-trolox equivalent antioxidant capacity coefficient. Graphical abstract

Design, Synthesis, Biological Evaluation, and Antioxidant and Cytotoxic Activity of Heteroatom-Substituted 1,4-Naphtho- and Benzoquinones

“…Antioxidant Capacity The newly synthesized compounds 4a, 5, 7a, 8, 9a, b, 10, 12, 14, 15, 17, 18 were screened for their antioxidant capacity by using the cupric-reducing antioxidant capacity (CUPRAC) methods 31,32) against trolox as the standard reference compound. The linear calibration equations of these compounds (as absorbance in a 1 cm cell vs. molar concentration) gave the molar absorption coefficient (ε) as the slope.…”

A method for dyeing polyester fibres with quinone derivatives and evaluation of their antioxidant activity

“…In addition, it is necessary that the range of novel biological active dyes is increased for the textile industry. In our previous study of new naphthoquinone derivatives, we have found that the synthesized S,S-and S,O-substituted 1,4-naphthoquinones exhibited good antioxidant activity [9] and strong color shades [10]. These encouraging results prompted us to extend the study on other S,S-substituted-1,4-naphthoquinones derivatives.…”

Potent Cytotoxicity of Novel L-Shaped Ortho-Quinone Analogs through Inducing Apoptosis

“…Therefore, we surmise that removing methyl at C-3 of the furan ring is more suitable for the binding site, and we anticipate that a novel L-shaped molecule without methyl at C-3 of the furan ring could provide better antitumor activities. Considering that some nitrogen, oxygen-substituted, and amino acid substrates can improve aqueous solubility and antitumor activities [21,22,23,24,25], we have attempted to introduce a great diversity of oxygen-substituted, nitrogen-containing groups and amino acids. Thus, in this work, we developed quinone-directed agents by removing methyl at C-3 of the furan ring and introducing a diverse side chain at C-2 of the furan ring, culminating in the discovery of a promising scaffold.…”